In the past, various methods for producing a saturated compound from an unsaturated hydrocarbon using hydrogen and for producing a new compound by hydrogenolysis of a hydrocarbon have been developed to be industrially utilized.
For example, Haber-Bosch process to obtain ammonia by reacting nitrogen and hydrogen in the presence of an iron catalyst under the condition of 20 atm and 500° C., a method for producing methanol from carbon monoxide and hydrogen at 50 to 100 atm in the presence of a catalyst such as copper oxide, a method for selectively hydrogenating a hydrocarbon such as acetylene and benzene, and a method for hydrocracking a hydrocarbon such as petroleum heavy oil and paraffin are exemplified. Recently, many technologies have been proposed, such as a method for hydrogenating a hydrocarbon by adding hydrogen in the presence of a catalyst such as molybdenum under high pressure (Patent Document 1), a method for synthesizing an olefin and the like from a normal paraffin and the like in the presence of a carrier obtained by supporting nickel, manganese and the like on a clay mineral under high pressure (Patent Document 2), a method for hydrocracking a hydrocarbon oil by using a catalyst which contains zeolite, silica-alumina and a metal (Patent Document 3), and a method for producing a higher hydrocarbon oil by hydrocracking a fat and oil (Patent Document 4).
In addition, recently, a technology for efficiently utilizing renewable sources with low environmental load has been necessary in terms of exhaustion of petroleum resources and climate change. A hydrogenation and a hydrogenolysis reaction of biomass resources have attracted attention as a technology for a renewable sources and future biorefinery. In particular, a carbon-carbon bond (C—C) and a carbon-oxygen bond (C—O) are cleaved by hydrogen in a hydrogenolysis reaction. A hydrogenolysis reaction can be effortlessly applied to the value chain of current chemical industry to be replaced, since a value-added core compound can be directly obtained by a hydrogenolysis reaction. In other words, the hydrogenation and a hydrogenolysis reaction of renewable sources may act as an intermediary between a currently available technology and a future biorefinery and have very high industrial value. For example, the intensive research for a hydrogenolysis of cellulose, glucose, glycerin, sugar alcohol or the like using a catalyst has been carried out (Non-patent Document 1).
Specifically, many methods have been proposed, such as a method for producing a hydrocarbon by preprocessing a biomass raw material such as cellulose in an alcohol and then carrying out a hydrogenolysis with a catalyst (Patent Document 5), a method for producing a sugar alcohol from cellulose under hydrogen-containing atmosphere and under pressure using a transition metal catalyst of 8 group to 11 group (Patent Document 6), a method for obtaining a reduced glycerin compound consisting of 1,2-propanediol, 1,3-propanediol, 1-propanol and 2-propanol with high selectivity by hydrogen reduction of glycerin in the presence of a catalyst (Patent Document 7), and a method for producing a hydrogenolysis compound such as butanediol by reacting 1,4-anhydroerythritol and hydrogen in the presence of a catalyst (Patent Document 8).